Ray  F. Middleman pittsburgh

Ray F. Middleman



Ray Middleman has a diverse and broad range of litigation skills, trying products liability cases for a crane manufacturer; non-competition cases for a home security company; Municipal Tort Claim Act cases for local authorities and municipalities; common carrier bus and taxi cases, some with multiple fatalities; construction claims; and shareholder rights litigation, among other civil litigation matters. Ray also has significant experience in defending both psychiatric and medical malpractice claims in the Western Pennsylvania area. During his 34-year career, Ray has tried approximately 50+ jury trials to verdict; 50-75 non-jury and administrative cases to verdict/decision; over 100 arbitrations; and mediated more than 20 cases to resolution.

In addition to significant trial work in state and federal courts in Pennsylvania and other jurisdictions, Ray has the unique experience of representing both purchasers and sellers in multi-million dollar transportation company acquisitions and in general corporate contracts with clients from a diverse array of industries and sectors.

Ray has worked with the Pennsylvania Public Utility Commission (PUC) for over 30 years on issues ranging from litigating fines and compliance matters to the preservation of the self-insurance status of the largest taxi company in the Commonwealth. He has appeared before the full PUC to testify on Transportation Network Company (TNC) issues and works with lobbyists in Harrisburg on multiple legislative initiatives. Ray was directly involved in drafting portions of the regulations affecting taxis, limousines and TNC operations in the Commonwealth.

Ray also helps companies draft employment agreements, employee handbooks, as well as bonus and incentive plans. In addition to defending U.S. Equal Employment Opportunity Commission (EEOC) and Pittsburgh Human Relations Commission (HRC) proceedings, he handles non-competition matters from negotiation and drafting of contract provisions through trial for breach of same.

In the oil and gas sector, Ray handles corporate and litigation matters including lease issues and leasehold development, pipeline disputes, and clearing title to oil and gas rights. He negotiates and drafts gas gathering agreements, joint venture agreements, and pipeline acquisition documents for a major oil and gas company in Pennsylvania.  He also litigates matters for an oil and gas support entity headquartered in Texas.

Representative Matters

  • Represented Purchaser in a $75 million gas pipeline acquisition, involving a joint-venture agreement and gas gathering agreement.
  • Represented Purchaser in the acquisition of a $10 million transportation company; also represented the same party when it sold the company several years later at a significant profit.
  • Represented a client in a series of cases involving the enforcement of a non-competition provision in an employment contract; successfully asserted that the covenants failed due to a lack of proper consideration.
  • Represented a bank in a Lanham Act case which successfully tried for three weeks in Federal District Court. Ultimate victory was preserved before the Third Circuit. Case eventually resolved in favor of the bank with a purchase of the name by the aggressor bank for a confidential amount.
  • Represented a timber company in an arbitration/administrative proceeding against the Department of Agriculture before the Civilian Board of Contract Appeals. Eventually obtained the return of $250,000 to the client and the negation of further obligation on a $4 million timber contract.
  • Represented a psychiatrist in a wrongful death action brought before the United States District Court for the Middle District of Pennsylvania. Obtained a defense verdict after a one-week trial.
  • Represented an insurance agency in an employment covenant violation involving encroachment and wrongdoing by two employees and a national insurance brokerage entity. Settled the case favorably after one week of trial for over $1 million.
  • Represented a psychiatrist and obtained a rare TRO from Common Pleas Court when the client refused to violate his oath to protect the sanctity of psychotherapeutic records. HMO had demanded access to review the records of several patients to confirm treatment plans and billing issues, terminating the psychiatrist when he refused to comply. Achieved full reinstatement of the psychiatrist without producing confidential records.
  • Represented an architect in a $20 million strip mall subsidence case. The architect was averred to have failed to note the results of carbonaceous soil testing. After seven years of litigation, obtained summary judgment for the architect.
  • Represented a common carrier to a summary judgment in a case in which a pedestrian was catastrophically injured when a taxi swerved off the road and crossed a sidewalk, pinning the pedestrian against a building.
  • Represented a common carrier to a defense verdict when a taxi left the roadway and crashed into the living room of a residence, injuring two people. Successfully used the “medical emergency” defense.
  • Represented a psychiatrist to a verdict/dismissal at trial in a case involving allegations of a lithium overdose with a teenage patient who sustained injuries from the overdose.
  • Represented a charter bus company in a head on double fatality with a pick-up truck in Venango County. Achieved a very favorable settlement after three days of trial and cross-examination of key plaintiff witnesses.
  • Represented defendant in multi-million dollar mediation regarding construction failures at the Pittsburgh International Airport Parking Garage Facility.
  • Represented common carrier defendants to multiple verdicts throughout the last 30 years.

Professional Affiliations

  • Pennsylvania Bar Association
  • Allegheny County Bar Association

Community Involvement

  • Reading is FUNdamental Pittsburgh, elementary school reading mentor
  • Lending Hearts Board Member

Awards and Recognition:

  • Attained an AV® Preeminent™ rating from Martindale-Hubbell

News and Insights


Legal Updates

Media Coverage

Speaking Engagements

  • “Pain and Suffering Damages in Personal Injury” and “Quantifying Pain and Suffering Damages” presenter for the National Business Institute program Pain and Suffering Damages in Personal Injury, April 2021.
  • “Metadata Explained,” presenter, National Business Institute, October 27, 2017.
  • “Raise the Sails! Taxi & Uber Transportation Issues,” speaker and panelist, National Conference of Regulatory Attorneys, June 2016.
  • “The ACA’s Impact on Medical Malpractice Litigation,” presenter, National Business Institute, May 2016.
  • “Damages in Personal Injury,” presenter, National Business Institute, April 2016.
  • “Advanced Trial Tactics,” presenter, National Business Institute, April 2015.
  • “Damages in Personal Injury,” presenter, National Business Institute, October 2014.
  • “Evidence and Expert Testimony,” presenter, National Business Institute, April 2014.


Ray enjoys racing in the American Endurance Racing series at classic racetracks throughout the Eastern Region.  He is an avid skier, hunter, golfer and enjoys travel.